Mechanisms and pathways from recent deoxysugar biosynthesis research

Current Opinion in Chemical Biology

Volumn 2, Issue 5, 1998, Pages 642-649

  Johnson, David A ^a   Liu, Hung Wen ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABEQUOSE; DEOXYRIBOSE; GLYCOSYLTRANSFERASE; HEXOSE; PARATOSE; TYVELOSE;

BIOSYNTHESIS; GENETICS; METABOLISM; REVIEW; SACCHAROPOLYSPORA; STREPTOMYCES;

DEOXYRIBOSE; GLYCOSYLTRANSFERASES; HEXOSES; SACCHAROPOLYSPORA; STREPTOMYCES;

EID: 0032174994     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(98)80096-3     Document Type: Article

References (42)

1. Varki A: Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 1993, 3:97-130.
2. Weymouth-Wilson AC: The role of carbohydrates in biologically active natural products. Nat Prod Rep 1997, 14:99-110. Comprehensive review of recent literature describing work aimed at determining the function of sugars in natural products, mostly antibiotics.
3. Kirschning A, Bechthold AF-W, Rohr J: Chemical and biochemical aspects of deoxysugars and deoxysugar oligosaccharides. Top Curr Chem 1997, 188:1-84. This is an exhaustive review of literature up to early 1996 pertaining to the mechanisms and genetics of deoxysugar biosynthesis, as well as organic and chemoenzymatic synthetic techniques.
4. Yu Y, Russell RN, Thorson JS, Liu L-d, Liu H-W: Mechanistic studies of the biosynthesis of 3,6-dideoxyhexoses in Yersinia pseudotuberculosis. J Biol Chem 1992, 267:5868-5875.
5. He X, Thorson JS, Liu H-W: Probing the coenzyme and substrate binding events of CDP-D-glucose 4,6-dehydratase: mechanistic implications. Biochemistry 1996, 35:4721-4731.
6. Liu H-W, Thorson JS, Miller VP, Kelley TM, Lei Y, Ploux O, He X, Yang D-y: Mechanistic studies of the biosynthesis of 3,6-dideoxysugars in bacteria: exploration of a novel C-O bond cleavage event. J Chin Chem Soc 1995, 42:627-636.
7. Lei Y, Ploux O, Liu H-W: Mechanistic studies on CDP-6-deoxy-L-threo-D-glycero-4-hexulose 3-dehydrase: identification of His-220 as the active-site base by chemical modification and site-directed mutagenesis. Biochemistry 1995, 34:4643-4654.
8. 3): two important enzymes involved in the biosynthesis of ascarylose. Biochemistry 1996, 35:7879-7889.
9. Gassner GT, Johnson DA, Liu H-W, Ballou DP: Kinetics of the reductive half-reaction of the iron-sulfur flavoenzyme CDP-6-deoxy-L-threo-D-glycero-4-hexulose-3-dehydrase reductase. Biochemistry 1996, 35:7752-7761.
10. 3). Biochemistry 1996, 35:16412-16420.
11. 6 as a redox cofactor: a new role for an old coenzyme? J Am Chem Soc 1993, 115:12177-12178.
12. Johnson DA, Gassner GT, Bandarian V, Ruzicka FJ, Ballou DP, Reed GH, Liu H-W: Kinetic characterization of an organic radical in the ascarylose biosynthetic pathway. Biochemistry 1996, 35:15846-15856.
13. 6 analog. J Am Chem Soc 1997, 119:1809-1817.
14. Thorson JS, Lo SF, Liu H-W: Molecular basis of 3,6-dideoxyhexose biosynthesis: elucidation of CDP-ascarylose biosynthetic genes and their relationship to other 3,6-dideoxyhexose pathways. J Am Chem Soc 1993, 115:5827-5829.
15. Thorson JS, Lo SF, Ploux O, He X, Liu H-W: Studies of the biosynthesis of 3,6-dideoxyhexoses: molecular cloning and characterization of the asc (ascarylose) region from Yersinia pseudotuberculosis serogroup VA. J Bacteriol 1994, 176:5483-5493.
16. Hallis TM, Lei Y, Que NLS, Liu H-W: Mechanistic studies of the biosynthesis of paratose: purification and characterization of CDP-paratose synthase. Biochemistry 1998, 37:4935-4945. The characterization of the first pure ketohexose reductase is described in this paper. Cytidine diphosphate paratose synthase is a new member of the short-chain dehydrogenase family and it utilizes a Theorell-Chance mechanism. This is likely to be the prototype enzyme for ketohexose reductases in deoxysugar biosynthesis.
17. Morgan PM, Sala RF, Tanner ME: Eliminations in the reactions catalyzed by UDP-N-acetylglucosamine 2-epimerase. J Am Chem Soc 1997, 119:10269-10277. This report on the mechanism of an epimerase in an aminosugar biosynthetic pathway is important because the epimerization occurs at a stereocenter with an unactivated proton. The intriguing mechanism proceeds via cleavage of the anomeric C-O bond, with 2-acetamidoglucal and uridine diphosphate as enzyme-bound intermediates. It is suggested that cationic eliminations via oxocarbenium intermediates are involved in the reaction.
18. Verma N, Reeves P: Identification and sequence of rfbS and rfbE, which determine antigenic specificity of group A and group D Salmonellae. J Bacteriol 1989, 171:5694-5701.
19. Rossmann MG, Liljas A, Brändén C-I, Banaszak LJ: Evolutionary and structural relationships among dehydrogenases. In The Enzymes, 3rd edn. Edited by Boyer PD. New York: Academic Press; 1975:61-102.
20. Gaisser S, Trefzer A, Stockert S, Kirschning A, Bechthold A: Cloning of an avilamycin biosynthetic gene cluster from Streptomyces viridochromogenes Tü57. J Bacteriol 1997, 179:6271-6278.
21. Lombó F, Siems K, Braña AF, Méndez C, Bindseil K, Salas JA: Cloning and insertional inactivation of Streptomyces argillaceus genes involved in the earliest steps of biosynthesis of the sugar moieties of the antitumor polyketide mithramycin. J Bacteriol 1997, 179:3354-3357.
22. Torkkell S, Ylihonko K, Hakala J, Skurnik M, Mäntsälä P: Characterization of Streptomyces nogalater genes encoding enzymes involved in glycosylation steps in nogalamycin biosynthesis. Mol Gen Genet 1997, 256:203-209.
23. Otten S, Gallo MA, Madduri K, Liu X, Hutchinson CR: Cloning and characterization of the Streptomyces peutetius dnmZUV genes encoding three enzymes required for biosynthesis of the daunorubicin precursor thymidine diphospho-L-daunosamine. J Bacteriol 1997, 179:4446-4450.
24. Gavini N, Hausman BS, Pulakat L, Schreiner RP, Williamson JA: Identification and mutational analysis of rfbG, the gene encoding CDP-D-glucose-4,6-dehydratase, isolated from free living soil bacterium Azotobacter vinelandii. Biochem Biophys Res Commun 1997, 240:153-161.
25. Mitchison M, Bulach DM, Vinh T, Rajakumar K, Faine S, Adler B: Identification and characterization of the dTDP-rhamnose biosynthesis and transfer genes of the lipopolysaccharide-related rfb locus in Leptospira interrogans serovar Copenhageni. J Bacteriol 1997, 179:1262-1267.
26. Tsukioka Y, Yamashita Y, Oho T, Nakano Y, Koga T: Biological function of the dTDP-rhamnose synthesis pathway in Streptococcus mutans. J Bacteriol 1997, 179:1126-1134.
27. Tsukioka Y, Yamashita Y, Nakano Y, Oho T, Koga T: Identification of a fourth gene involved in dTDP-rhamnose synthesis in Streptococcus mutans. J Bacteriol 1997, 179:4411-4414.
28. Ahlert J, Distler J, Mansouri K, Piepersberg W: Identification of stsC, the gene encoding the L-glutamine: scyllo-inosose aminotransferase from streptomycin-producing Streptomycetes. Arch Microbiol 1997, 168:102-113. Reported herein are the identification of eight new genes, strO-stsABCDEFG, in the cluster that encodes proteins for streptomycin production in Streptomyces griseus. Two proteins, StsA and StsC, are members of a new class of pyridoxal 5′-phosphate-dependent aminotransferases. StsC was purified, and its aminotransferase activity was demonstrated. This is the first report ascertaining the aminotransferase activity of this class of enzyme.
29. ••], this paper represents a significant leap forward in our understanding of deoxysugar biosynthesis.
30. ••], this paper represents a significant leap forward in our understanding of deoxysugar biosynthesis.
31. Gandecha AR, Large SL, Cundliffe E: Analysis of four tylosin biosynthetic genes from the tylLM region of the Streptomyces fradiae genome. Gene 1997, 184:197-203. Of the four genes analyzed in this paper, two of them encode a glycosyltransferase (tylM2) and a methyltransferase (tylM1) that are involved in the biosynthesis of mycaminose, one of the deoxysugars in tylosin. A reasonable biosynthetic route to mycaminose is proposed.
32. Gallo MA, Ward J, Hutchinson CR: The dnrM gene in Streptomyces peucetius contains a naturally occurring frameshift mutation that is suppressed by another locus outside of the daunorubicin-production gene cluster. Microbiology 1996, 142:269-275.
33. 1 locus, which controls daunorubicin biosynthesis in Streptomyces peucetius. J Bacteriol 1995, 177:1208-1215.
34. Thorson JS, Lo SF, Liu H-W, Hutchinson CR: Biosynthesis of 3,6-dideoxyhexoses: new mechanistic reflections upon 2,6-dideoxy, 4,6-dideoxy, and amino sugar construction. J Am Chem Soc 1993, 115:6993-6994.
35. Otten SL, Liu X, Ferguson J, Hutchinson CR: Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyl transferase involved in daunorubicin biosynthesis. J Bacteriol 1995, 177:6688-6692.
36. Scotti C, Hutchinson CR: Enhanced antibiotic production by manipulation of the Streptomyces peucetius dnrH and dnmT genes involved in doxorubicin (adriamycin) biosynthesis. J Bacteriol 1996, 178:7316-7321.
37. Liu H-W, Thorson JS: Pathways and mechanisms in the biogenesis of novel deoxysugars by bacteria. Annu Rev Microbiol 1994, 48:223-256.
38. Jacobsen JR, Hutchinson CR, Cane DE, Khosla C: Precursor-directed biosynthesis of erythromycin analogs by an engineered polyketide synthase. Science 1997, 277:367-369.
39. Marsden AFA, Wilkinson B, Cortés J, Dunster NJ, Staunton J, Leadlay PF: Engineering broader specificity into an antibiotic-producing polyketide synthase. Science 1998, 279:199-201.
40. Solenberg PJ, Matsushima P, Stack DR, Wilkie SC, Thompson RC, Baltz RH: Production of hybrid glycopeptide antibiotics in vitro and in Streptomyces toyocaensis. Chem Biol 1997, 4:195-202. Cloned glycosyltransferases from glycopeptide antibiotic producers were used to produce novel hybrid antibiotics, both in vitro and in vivo. This is one of the first reports on the use of sugar biosynthetic genes to produce new compounds, and it underscores the future potential of utilizing glycosyltransferases to create valuable drugs.
41. Madduri K, Kennedy J, Rivola G, Inventi-Solari A, Filippini S, Zanuso G, Colombo A L, Gewain KM, Occi JL, MacNeil DJ, Hutchinson CR: Production of the antitumor drug epirubicin (4′-epidoxorubicin) and its precursor by a genetically engineered strain of Streptomyces peucetius. Nat Biotechnol 1998, 16:69-74. A fermentation method for producing 4′-epidoxorubicin is reported in this paper. The method involves cloning heterologous Streptomyces avermitilis avrE or Saccharopo/yspora eryBIV genes into an S. peucetius dnmV mutant blocked in the biosynthesis of daunosamine. These experiments not only unambiguously assigned AvrE and EryBIV as ketohexose reductases, but they also clearly demonstrated that combinatorial biosynthesis with deoxysugar biosynthetic genes can be used to generate valuable hybrid antibiotics.
42. Stubbe J, van der Donk W: Protein radicals in enzyme catalysis. Chem Rev 1998, 98:705-762.